32 Things To Ask Someone To Have A Better Conversation

We all know the basic formula for meeting somebody new.

“Hi, I’m X, nice to meet you.”
“Nice to meet you X, I’m Y.”
“Nice to meet you too Y. How are you doing today?”
“I’m doing great X! How about you?”
“I’m good thanks! So, Y, what do you do for a living?”

I don’t know about you but most of the time being asked or asking someone what they do for a living can be the end to a conversation. You politely ask the question, they rely with their most used answer from their ‘basic conversation’ mind vault, and you either ask them a question following the response; “Oh that’s interesting, what does that entail?” or the conversation drops dead.

It’s boring and must be stopped.

The asked probably doesn’t even like their job, in fact the asker probably doesn’t like their job, so why ask? It seems to be a staple question when conversing with somebody new or when being interviewed by your extended family at a reunion – but I think we should dare to mix things up a bit, and here’s what to ask them instead:

  1. What is your ultimate goal in life?
  2. What do you do outside of work?
  3. How do you like living in this city/town/village?
  4. What creative things do you enjoy?
  5. Are you learning any new skills at the moment?
  6. Would you ever want to run your own business?
  7. Where’s your favourite place to get away from it all and de-stress?
  8. If you could go anywhere right now, where would you go?
  9. What’s your favourite memory?
  10. What did you want to be when you were a kid?
  11. If money wasn’t a worry, what would you do with your days?
  12. What has been your biggest challenge in life?
  13. Which author inspires you the most?
  14. What decade do you think you could have thrived in better than this one?
  15. What book have you not been able to put down recently?
  16. How do you make time for yourself?
  17. Have you ever done something for charity?
  18. What was the last random act of kindness you witnessed?
  19. If a TV show was your reality, which show would you chose?
  20. What was the best year of your life so far?
  21. Would your childhood self be proud of you?
  22. What is your most proud moment?
  23. Why did you chose to do the job you do?
  24. Who do you most admire?
  25. What is your passion?
  26. If you wrote a autobiography, what would you call it?
  27. Which actor would play you in a movie of your life?
  28. What was your least favourite job?
  29. What is something you wish you had done but didn’t?
  30. What is something you are glad you didn’t do though you had the opportunity?
  31. What was the last thing you were happy to quit doing?
  32. What is the most exciting thing coming up for you?

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